Think Tank: The Princess Bride and The Dread Pirate Roberts

Think Tank: The Princess Bride and The Dread Pirate Roberts

Exactly how dread is the dread pirate roberts?

Belinkie: Okay, so Westley spends a few years pretending to be the Dread Pirate Roberts. Can we then assume that Westley has killed hundreds of innocent people? Isn’t it well-established that the Dread Pirate Roberts never takes prisoners? Isn’t the real story of the Princess Bride about a man who becomes a monster in order to survive? It’s basically the Black Freighter story from Watchmen – he gets back to his beloved, but by all rights, she should be horrified by him. Westley is LITERALLY the most depised man in the entire world. It would be like if he spent the last three years running Al-Qaeda.

Now keep in mind, I haven’t read the novel for a long long time. Anyone know it well?

Mlawski: I haven’t read the book in a while, but I just flipped to the section where Buttercup realizes that the man in black is Westley, and she doesn’t have any problem with it. He says, “As you wish,” and she’s like, “YAAYAYYYYYYY!” Basically just like it happens in the movie.

This has always bugged me a little, too. But then, I was also upset when Westley let Vizzini drink that iocane stuff. Wallace Shawn must live!

Belinkie: You could probably write a really funny sketch that takes place immediately after the movie ends, where Buttercup starts to ask Westley a little about his adventures. He tells her the most horrible stories imaginable in this wistful tone.

“Sometimes I miss the sunset over the waves, the cry of the seagulls, and the simple pleasure of having my way with a schoolgirl and making her parents watch.”

“Excuse me?”

“I was thinking of you every second, my dearest!”


Perich: I think we can assume that Westley has cultivated a reputation for being a mass-murderer. But that doesn’t necessarily mean he is one. After all, the grapevine of reputation in The Princess Bride is so inefficient that nobody knows the Dread Pirate Roberts changes his appearance every X years.

Lee: We actually see something similar with the phenomenon of modern day Somali piracy. The public perception of ruthless pirates out for blood on the high seas is pretty far from the reality, which is that it’s all fairly business-like. The pirates have no real incentive to kill hostages, plunder loot, or otherwise cause trouble; instead, they basically seize a ship and wait for the shipping company to get a professional negotiator to broker a deal at market rates…with the professional negotiator that the pirates also hired.

As you wish.

One can only assume that the Dread Pirate Roberts was likewise primarily interested in protecting one of his most valuable assets: his reputation for brutality.

Fenzel: It’s a fantasy – in a fantasy, it is okay, even desirable, for a man to have done a whole lot of really bad shit, provided he is the most desirable man in the story – and as long as he shows signs he can be redeemed, and keeps it somewhat decorous in the presence of ladies, so to speak.

This is why Greedo shooting first is so bad. We don’t blame Han for shooting first. Nobody has to make exuses for Han Solo. By making Greedo shoot first, Lucas immasculates him.

Yeah, take it out of the context of fantasy, show the innocent victims of the Kessel spice trade, show all the people the Dread Pirate Roberts murdered, and you make him less attractive, but it’s important to note that we want to deny these things. We want to not care these guys are murderers.

And women especially want it – to illegitimize it is to illegitimize a very large sector of very legitimate sexual fantasy.

I’d put this in the “human beings aren’t essentially good, despite our attempts to demonstrate the contrary” bucket.

Stokes: Whuuuuut? Are you suggesting that Wesley is really more desirable than Inigo? Because that is not how my swash is buckled. (Although Inigo too has done his share of dirt, I suppose.)

Perich: So let’s examine for the moment this notion of “women want the bad boy.”

Let’s not get into the whole evolutionary psychology angle, because that’s a foggy road with as many bad turns as good ones. But it’s indisputable that pop culture throws a lot of attractive bad boys at female audiences. The guy in the leather jacket, leaning on his motorcycle. The unshaven man in the pool hall. James Dean, early Johnny Depp, young Charlie Sheen, Clive Owen, James Bond, Severus Snape, etc.

Taking for granted that “the attractive bad boy” is a powerful trope, is Wesley either the pinnacle of that ideal or a satire of it? Is he the Siddhartha or a caricature (Roger Zelazny’s Mahasamatman), to put it cleverly?

On the one hand, Wesley is bad to Buttercup for no reason. He yanks her along by the wrist, calls her mean things and intimates that her love was false. Only when she gets the upper hand on him by pushing him down a hill does he reveal his trump card: hey, I’m that guy you loved! To use a wrestling metaphor: she reverses his position, only for him to reverse her again and end up back on top. By making her, um, weak in the knees (metaphor failing, EJECT EJECT).

So Wesley seems like an unnaturally dark bad boy. He doesn’t just go from callous to lukewarm, the typical bad boy arc. He goes from malevolent to compassionate.

On the other hand, Wesley and Buttercup are both comical people. The book establishes this better than the movie. They’re both a little silly and, when under the effects of love, they can act kind of dumb. So maybe Wesley’s heel-turn/face-turn routine isn’t meant to be calculated – it’s what a silly man thinks is the right idea at the time. Perhaps Goldman, as author, is using Wesley as another comical exaggeration. I’ve already given you the strongest giant in the world, he says, and the greatest swordfighter in the world. Now here’s the most seductive bad boy in the world! BLAM!

Mlawski: Why are we talking about women wanting the bad boy? Are we implying here that adult women are the target audience of The Princess Bride, and that Westley was designed primarily to be attractive to them? Because I’m not at all sure that is the case. The movie version is framed as a story by an old man for a little boy, so I think it’s fair to say that, in the world of the film, anyway, Westley is designed to be attractive to Fred Savage.

It’s like Han Solo. I’d argue that Han Solo was designed to be attractive to young boys, because they were the target audience of Star Wars. The fact that the females found Han attractive, I think, was gravy. But I personally know a lot more men than women who are in love with good ol’ Han.

The idea that “all women want the bad boy” is quite overstated, I think. For one thing, it’s not always true — when I was a wee lass, I had a crush on Luke, not Han — but, yeah, I was a strange child. For another thing, “bad boy” is a badly-defined term. Speaking for myself and not all women, I can say the fantasy characters I tend to find most attractive are the ones who have some edge — the unshaven face and leather jackets Perich was talking about — but who are ultimately good. (Aragorn and Han being the ultimate fantasy examples; Rick Blaine being the ultimate non-fantasy example.) (Mmm.)

Han shooting Greedo doesn’t undo Han’s inherent goodness, because Greedo is a Bad Guy. (Might as well say that Obi Wan was Bad because he cut a guy’s arm off in a bar.) Other than shooting first, what does Han do to make him a “bad boy”? He’s a religious skeptic, and he doesn’t immediately jump to action to save the day. OK, he’s a smuggler, too, but a smuggler in an Evil Empire, which on the fantasy criminal hierarchy is about as evil as selling pot to your neighbor. D&D-wise, I’d argue all of this puts Han in True Neutral territory at the beginning of Episode IV. By the end of Episode IV, he’s solidly Neutral Good or possibly Chaotic Good. He’s an anti-hero who leans hard toward the hero side of the equation. And anti-heroes of this type are still heroes. Otherwise, we’d call them anti-something elses.

As far as Princess Bride is concered, yeah, Inigo over Westley any day. But then, none of the dudes in that film do much for me.

Shechner: Might I remind you that said film features a six fingered Christopher Guest?

Six fingers, Shana. Imagine the possibilities.

Mlawski: I did consider him, but I thought you’d all judge me poorly if I mentioned it.

Perich: This is for posterity, Shana. Please, be honest.

Mlawski: In a fuck/marry/kill situation, I think I’d have to say Six Fingered Man/Inigo/Humperdick.


Lee: Side note: Christopher Guest is the owner of two significant moments of “augmentation by one” in movies: “six fingered man” and “these go to eleven.” The next major player in this category is the three-boobed woman from “Total Recall,” which puts Guest in rarefied territory.

[And that’s where we left it, Overthinkers – on a Paul Verhoeven movie, surprise surprise. But where will you take it? Was the Dread Pirate Roberts really a dire murderer? Did Buttercup make the right call? Sound off in the comments!]

34 Comments on “Think Tank: The Princess Bride and The Dread Pirate Roberts”

  1. Tulse #

    Huge props to John Perich for the Lord of Light reference, which is (I think) Zelazny’s best book by far.

    And huge props to Mark Lee for inventing out of whole cloth the category of “augmentation by one”, which is begging for further examples. The one that comes to mind most readily is an earlier version of Total Recall example — in Man with the Golden Gun, James Bond impersonates the assassin Scaramanga by having a fake third nipple attached to his chest (one of the weirdest tropes ever in a Bond film).


  2. Isaac #

    I think it’s important to point out that Westley wasn’t so much pretending to be the Dread Pirate Roberts as filling the role of Dread Pirate Roberts. It’s not quite the same thing. By the time he assumes the role, there’s no “authentic” Roberts to masquerade as; by putting on the outfit and the cruel behavior, he becomes Roberts. In that way, the Dread Pirate Roberts is sort of like the Pope.

    (It’s a title or an office, not a person.)

    As for “augmentation by one”: let’s not forget Zaphod Beeblebrox.


  3. Jesse M #

    Wesley leans on a variation of the “bad boy” trope, which is the good-boy-bad-reputation archetype. The other obvious example of this is Patrick from 10 Things I Hate About You. In 10 Things, Ledger’s character was finally explained: his mysterious absence was due to his taking care of his grandmother, or something like that. I think, though it’s not explicit in Princess Bride, the same phenomenon is implied: that rumors of grave evil have swirled around Wesley, but they’re greatly exaggerated. He’s not actually a murderer or a sociopath — he’s just a lovable rogue who occasionally (e.g. in the case of Vizzini) does what needs to be done.

    In fact, I think almost all idolized bad boys are implied not to be evil, but rather misunderstood. Action movies like Boondock Saints may be blurring the line between “evil” and “awesome,” but I still never remember seeing a sexually desirable but truly evil protagonist in a film. One of the most interesting cases is Trigun, wherein the main character, Vash, has a reputation for being an evil bandit, but this is due to two things: his propensity for property damage, and one very unfortunate incident where he accidentally mishandled a great power that was placed in his care. He’s got a reputation for being evil, but he’s actually just clumsy on a cosmic scale. There’s still a very good guilt sub-plot, and a fascinating theme about how his reputation keeps him safe, but eventually draws him into the role he so despises: the role of murderous enforcer.

    My assumption, which is that Wesley is actually innocent, and is just the victim (or beneficiary) of hearsay has some interesting implications. Like, the scene on the hill is no longer a matter of Buttercup forgiving Wesley’s sins… rather, it’s a matter of seeing through his shroud of reputation, because she knows him better than that. Maybe this is a bit strong of an assumption to make so suddenly, but hey, sometimes the mind does that.

    Great discussion! Interesting angle on Wesley’s strange life.


  4. Sylvia #

    Gah! Pete! Why does every nerd debate turn into Greedo shot first?

    ANYWAY. Mlawski references an interesting girl crush phenomenon, when we’re little we tend to go for the pretty boy (Luke) but as we get older we start to be intrigued by the bad boy (Han). So, it makes sense that Buttercup starts off liking Farmboy Wesley and then is into Pirate Wesley.

    But is Wesley a mass-murderer? Well, it’s all about image so it’s possible that he himself did not murder any ship he attacked, but ordered his crew to do it. Which introduces a whole new moral dilemma. Also, does Wesley suffer from any survivor’s guilt?

    Would the precurser to “augmentation by one” be Victor Borge’s “Inflationary Language”? Elevennins anytwo?


    • Tulse #

      Would the precurser to “augmentation by one” be Victor Borge’s “Inflationary Language”?

      Fantastic! Thanks for that!


  5. Adrian #

    “Never takes prisoners” is not the same thing as “kills every motherfucker on the boat.” Everyone always surrenders to Roberts because of his reputation, and then he takes their stuff and lets them live. If they thought he killed everyone no matter what, no one would surrender. Their assumption is that he never takes prisoners *in a fight*.

    Since The Princess Bride is really more of a fairy tale than a fantasy, and runs on a sort of Douglas-Adams-logic, I think we can take the story at face value that this works 100% of the time, and Westley hasn’t murdered anyone.

    Of course this all completely ignores the fact that he’s been ripping seafarers off for years, but I think that just gets filed under Pirates Are Kewl.


    • Tom #

      This. There’s a book about the economics of pirates called The Invisible Hook. I can’t recommend it unequivocally, but it makes a very interesting argument about the reputation of pirates generally as bloodthirsty marauders. As long as everybody on the ship being ordered to surrender believes that they will be killed if they fight, they will always surrender to avoid it. (Especially because the common sailors on the ship don’t have a real incentive to defend the cargo; they get paid almost the same whether they get overtaken by pirates or not.)

      The Dread Pirate Roberts is an extreme case of this general proposition. At some point, the original DPR must have cut off more than his share of sailors’ heads; however, at the point that the story takes place everybody is smart enough to give him (them) a wide berth.

      (This, of course, makes getting on the DPR’s ship a plum gig for any prospective pirate, so he can pick from the best of them; this only enhances his image as somebody who will slaughter anybody who gets in his way.)


  6. Del #

    You missed a vital point: When Westley is emotionally torturing Buttercup after saving her from Vizzini, he is just probing her, trying to determine if her love for him survived his five-year sojourn, and he’s trying to figure out if she still loves him, and if so, why she is marrying another man.


    • Jason Knox #

      I think this is key – it’s not some mere curiosity on his part. To hear that your true love is betrothed to another causes a wound – “Life is pain!”

      He didn’t just flip a switch as he was tumbling down the hill. At the bottom of the hill he still persists, just in a slightly different tone, “I told you, ‘I would always come for you.’ Why didn’t you wait for me?” To say that Westley had a score to settle would be saying it wrongly, but it is fair to say that Buttercup had to learn an important lesson – that unfaithfulness to true love is worse than death and causes a wound that can not be ignored.

      This is not a malevolent villain, but a wounded lover willing to pay her debt himself if she still loved him.


  7. funkycatullus #

    What about the way the movie sets up Inigo as the next Dread Pirate Roberts? Westley had a good reason to assume the role–he owed his life to the previous DPR, and had an opportunity to help him retire to a peaceable existence. Are we happy to see the lovable Inigo leave the revenge business to become a heartless marauder? They decided it so nonchalantly.


  8. Jamas Enright #

    Never really clicked with PB as a movie that captivated me, unlike plenty of other people in this post. Is this because I didn’t see until I was around 20 or so? Don’t know, but it has failed to sear itself into my memory…

    On the other hand, cf Captain Shakespeare from Stardust. “Ah, don’t mention it. Seriously, don’t mention it…you know reputations, lifetimes to build, seconds to destroy.”


  9. cat #

    Others have already addressed what I see as misreadings (“I think we can assume that Westley has cultivated a reputation for being a mass-murderer. But that doesn’t necessarily mean he is one.” and “he is just probing her, trying to determine if her love for him survived his five-year sojourn”) so I will turn my attention to the question of the not-really-bad bad boy and a female audience still being attracted to a legitimately bad/scarred character.

    As a consumer of a vast amount of “romantic” media, I would definitely agree with the idea that a great deal of the romantic leading men out there with any darkness to their characters usually have that written out or dealt with by act 3. Either, they haven’t done the awful thing you think they have, the misconception is cleared up, or you’re given a sufficient reason to forgive them for it. This is the model of many a book, film, and romance novel. Otherwise, why would writers waste valuable time always explaining and/or excusing the behavior of these men? If we truly weren’t meant to care that Wesley might have killed many while marauding and pillaging then he wouldn’t have to explain to Buttercup as they went through the woods about how he became the DPR. Implicit in his explanation is the feeling that he doesn’t relish any of the violence of his job and probably doesn’t encounter a lot with the way he describes it. When these heroes are meant to get our sympathy they usually detail all the bad they’ve done and are then promptly forgiven because of the honorable reasons they had for doing it. Speaking of violence, Wesley’s mode of fighting plays into this idea. There’s a lot of gallant fencing mixed with clever intimidation. There aren’t too many prolonged fights where someone is shown to be wounded or hurt the way they play out Mandy Patinkin’s fight.

    “On the one hand, Wesley is bad to Buttercup for no reason. He yanks her along by the wrist, calls her mean things and intimates that her love was false. Only when she gets the upper hand on him by pushing him down a hill does he reveal his trump card: hey, I’m that guy you loved!”
    Again, I agree with what’s been said. It’s been a while since I’ve seen the movie but I don’t remember him saying anything too awful aside from criticizing her faithlessness to the man who loved her so intensely. Given his hurt at the news that she was getting married it’s fairly understandable. That, or I’ve just been conditioned to callous behavior from arrogant males as part of a continuum that ranges from acceptable to romantic.


  10. SQ_Minion #

    It’s possible that a trump card is being used to justify all of Westley’s actions–that is, “true love”. True love is used in the Princess Bride as the Ultimate Good, and thus any action driven by true love must be inherently good–even killing hundreds of innocent people. In this fable the only two people that really matter are the two lovers, and so their fates determine the morality of the story. As for Westley’s rough treatment of Buttercup after Vezzini’s death, it always seemed to me as though Westley was testing Buttercup, making sure her heart had stayed true. Now, in my opinion this test should not have been necessary; true love should have provided the necessary trust. Nonetheless, Westley did have some reason to feel that Buttercup’s loyalty should be tried. She was to marry Humperdick, after all. So, in this I would agree with Del’s above statement with the exception that I would not classify it as “torture”. The Machine is torture; a temporary rudeness is not.


  11. Caroline #

    I feel like a lot of people are gliding over the Dread Pirate Roberts murder thing. If Westley is DPR and doesn’t kill everyone his ship captures, he’s the first. After all, the only reason he initially survived was his intriguing “please.” Everyone else on the boat with him was killed. And then he spent years hearing “I’ll most likely kill you in the morning.” The DPR crew is most definitely a crew of murder-happy pirates.

    However, when Westley comes for Buttercup, there’s no saying how long he’s been DPR. He spent most of the time he was gone learning the pirate trade and building up his resistance to iocane powder. It’s possible that the DPR he inherited the title from only just retired, and Westley had not yet gotten around to seizing ships and ordering executions when he came for Buttercup.

    Although… since he was working for the pirates all that time he probably participated on some level in the murdering before taking the title. So there’s almost certainly blood on those farm boy hands.

    They don’t really say what kind of ships the DPR targets, so I guess we pretend they only go after the ships with bad people…. but that’s kind of weak.

    As to the “bad boys = sexy for ladies” thing: it’s true that I personally tend to be drawn to the “bad boy” or at least “loveable rake” characters in fiction. Your Han Solos, Westleys etc. But not because they’re bad; because they’re funny! They’re clever, cocky, have the best lines, are useful in an emergency, and never mope in the face of adversity. (e.g. Han was smarting off as he was being frozen in carbonite, and Westley has sarcasm in the face of paralysis and almost certain defeat!) I don’t know if it’s necessarily true that ladies love outlaws, but I know I love confidence and a rapier wit.


    • Claire #

      Totally agree with the last bit. Think about male characters in movies that are funny and confident. Now think about male characters in movies that aren’t remotely bad/evil. Make a mental venn diagram of these two things. If they overlap, please tell me.

      Poor Buttercup. When I think about it every man who crosses her path is either extremely violent or incredibly old.


      • Paul #

        Beuller….Beuller? He defies authority and gets up to shenanigans, but he isn’t really bad.

        Phillip Marlowe in The Big Sleep. He exudes confidence and has a quick wit to keep everyone he talks to on their toes.

        Tom Destry Jr. from Destry Rides Again. Jimmy Stewart is the upstanding law man who uses words to greater effect than any gun.

        I was thinking Cary Grant’s Roger Thornhill from North by Northwest, but then I remembered that he was an ad executive. Clearly evil.


        • Caroline #

          You do get it a lot in older movies – Humphrey Bogart’s characters in both Casablanca and the Maltese Falcon were amazing. “My guesses may be excellent or they may be crummy, but Mrs. Spade didn’t raise any children dippy enough to make guesses in front of a district attorney, an assistant district attorney, and a stenographer.” Plus there’s Errol Flynn in like… all his movies. Nick Charles in The Thin Man series.

          Robert Redford and Paul Newman combined a couple of times (Butch Cassidy and the Sundance Kid, The Sting) to share excellent dialogue and good humor (and die… that one time). But also Paul Newman in Cool Hand Luke.

          In most of these examples, the characters are either outlaws (Westley, Robin Hood, Butch and Sundance, Han Solo, etc), or operate parallel to the law (Sam Spade, Nick Charles, and Phillip Marlowe, for example, are all detectives who sometimes work with the police, but they aren’t the police). And a lot of them do some bad things. But the bad things they do never compromise what we love about their characters, since we never liked them for being paragons of virtue – we liked them for living their way with no apologies.


          • cat #

            “Think about male characters in movies that are funny and confident. Now think about male characters in movies that aren’t remotely bad/evil. Make a mental venn diagram of these two things. If they overlap, please tell me.”

            I don’t think you can have a character that’s always funny and confident if you want him/her to have any depth. I don’t think you can have a character that isn’t remotely bad/evil without him/her being flat. That character would have to never say a mean-spirited thing, have a negative thought, tell a lie, fight the villain. I suppose boy-scout Superman counts but throwing people into buildings is not exactly something “good” people do, even if it’s for the right reasons. It’s violent and it causes property damage.

            Leaving that aside, there are a whole host of male characters that are funny and confident (except when the situation is serious) who are also good guys. Acting like a jerk sometimes doesn’t make you a bad guy. And acting like a jerk is sometimes necessary for sarcasm and humor.

  12. chris strange #

    1. We know that he spent quite some time as the Dread Pirate Roberts.
    2. We know that Dread Pirate Roberts has a reputaion that the kills everybody that he captures.
    3. We know that the previous Dread Pirate Roberts killed everybody except Westley.
    4. We know that nobody really know about the switch between the previous DPR and DPR Westley

    In order for that last part to be possible he must have continued the previous DPR’s modus operendi, and that there are no witnesses willing, or alive, to tell that the DPR is now suddenly a different person. Both of these lead to the conclusion that Westley’s time as DPR has been as much as a kill crazy rampage as the last one’s was.

    This means that there is an alternative scenario. He is not an unfortunate forced into wicked ways by fate then saved by love. He is a mass murderer, and he liked it. However the heat has got too much. The world knows him and his reputation, and is out to get him before he gets them. So he needs a place to lie low for a while and a patsy to take the fall. He decides that the only person that would be willing to set aside his many terrible crimes would be is old flame. He tests Buttercup to make sure that she is still useful for him and packs Inigo off to a certain death, then waits. A few years later with Inigo’s mutilated body on display in a gibet under a sign saying ‘Dread Pirate Roberts’ he decides it is time to go back to sea. So rapes his new family to death before sewing their skins into a war canoe and begins his reign of terror afresh. At least that is what I want the sequal to be, simply so that I can watch the traumatised movie goers stumbling out of the cinema.


    • Matthew Belinkie OTI Staff #

      “Grandpa, maybe you could come over and read it again to me tomorrow?”


    • Samuel Segrist #

      Is it possible that the Dread Pirate Roberts narrative is an extended metaphor for wanton, promiscuous, sexual wandering on the part of Westley who at the beginning of the story has found his true love in Buttercup, but still has oats to sow. After five years of “lady-killing” and sexual marauding, he eventually returns for a life of monogamy, but to patch things up with Buttercup, Westley claims that he “detested” all the “violence.”


      • cat #

        Ooo, I like that theory. It also fits in with the “lovable rake” storyline where a man is free to go gallivanting around with all the women he likes as long as he settles down to monogamy and true love in the end. They didn’t mean anything/It wasn’t true love except with you. In fact, all of that “lady-killing” adds to his character, both with the male and female (which is odd) audience. It just makes him seem more appealing as in my mind, the typical romantic hero has to be intelligent, capable, attractive, and somewhat charming. All that “sexual marauding” just makes him seem more capable. There are probably a lot of things that are wrong with that conclusion but let’s bracket that for another day.


  13. Gab #

    As a woman, allow me to put in my two cents on the Bad Boy mystique- and keep in mind this is my take and not meant to speak for anyone else. I’d have to say there’s some truth to it, but the attraction is more, shall we say, carnal. A man that acts like an asshole, even if he’s hiding a soft interior, is ultimately unappealing. Villains can be extremely sexy (like Alan Rickman in pretty much any of his villainous roles) (although even in his non-villainous roles, he makes me swoon, but I digress), but it’s a fleeting, superficial feeling. Perhaps the notion of some passionate, heated moment is intriguing, but that’s not the kind of man I’d be interested in coming home to (or whatever, you know what I mean). However, there is a difference between “gruff” and “bad,” I think. Aragorn, for example, is extremely manly, but he’s certainly not a jerk, and there is never a question of his integrity or inherently good nature- so he’s the man I have always had the hots for, from that example pool. Sure, Legolas never falters in the eyes of the Ethics Committe, either, but I don’t think I could be very serious with a man whose hair is always prettier than mine.

    As for Westley’s potentially bloody hands: I am of the camp that takes high stock in the wording. I haven’t read the book in ages (and the differences do abound, not to mention the extra Fezzik story… sniffle), but the wording in the movie is “never takes any prisoners.” Or, if not that exactly, “kill” is never directly used. The implication there is that yes, indeed, he gets away with not actually killing anybody because they don’t bother trying to resist for fear of death. Remember, he says, “No one would surrender to the Dread Pirate Westley.” “Surrender” is the important word, there. As for the, “I’ll probably kill you in the morning,” from the previous Roberts, I think it was just the previous dude putting on airs. If Westley has to play the part in his “cruelty” (to use Buttercup’s diction), it makes sense his predecessor would have, as well. I doubt there was ever an intent to kill Westley.

    I’m also in the he-was-testing-her-camp, too. While he probably didn’t think in his heart of hearts his twu wuv would betray him, he didn’t know all of the details of the marriage- who could? So he had to be sure, and he used the reputation of his role to mask that test.

    Oh, and about Inigo. It may have come across as rather insufficiently debated in his head in the movie- he gets the offer, nods, and then jumps- but he had already realized there was nothing else for him to do with his life, and, presumably, had been contemplating this notion since the moment he stabbed Count Rugen*. So it isn’t a stretch to think he’d jump at a lucrative business opportunity.

    *The silence in that moment is resonant (hah!) of the emptiness created in Inigo’s life after completing his mission. This is an example of how the absence of music can sometimes make a scene even more profound than if a bit of score was heard in the background.


    • Caroline #

      Well, ACTUALLY…. the wording in the movie is “Never left captives alive.” Westley also explains that he was only spared because of the “please,” meaning everyone else on his ship actually was murdered. At the very least the original Roberts, the Roberts before Ryan, and Ryan were murderers.

      And Westley, when in his mask, tells Buttercup, “I kill a lot of people.” He may have been messing with her, but there seems to be a lot of evidence that part was true.


      • Caroline #

        Cummberbund! Roberts, Cummberbund, and Ryan are all confirmed murders.


  14. Greg #

    Wait a minute. Let’s take a moment and reexamine the “takes no prisoners” assumption. The fact is that in the quasi medieval world in which PB takes place, you don’t get a reputation for exterminating shiploads of people. You get it by making sure you get enough people home safely to tell your story. Since Westly makes it quite obvious that the reputation is the key to the whole game, is may be that the DPR simply leads a crew of masterful showmen and PR people who make a great show of running on board your ship, making a great deal of noise pretending to gruesomely murder people and then dropping the “survivors” in critical population centers.

    If I remember correctly, Westly says that the crew was oblivious to the DPR succession, but not that they didn’t understand the game. This theory is of course reinforced by Westly solving immediately going to theatrics to solve a lot of his problems rather than murder… the holocaust cloak, “to the pain.” He demonstrates a keen understanding of performance and the manipulation of human emotion.

    ** Novel spoilers follow **

    Goldman frames his novel as a condensation of an older larger novel from which he trimmed the more boring parts. Since it seems like the DPR killing and marauding must have been included the the theoretical original novel and that could not have a boring part, I am inclined to believe that the “cut” portion contained a lot of PR strategizing, grotesque dummy building, rumor spreading in taverns, and minimal actual marauding.

    However, it is also important to remember that the central theme of the novel is that true love is a stupid impossible thing and that the whole Westly/Buttercup story is a mockery of this romanticized vision. In the book, this is expressed constantly as Goldman relates his (ficticious) frustrations with his home life throughout the book. So if Westly did go around killing tons of people and Buttercup takes him back because of “true love,” it does further illustrate the point that this “true love” notion is a dumb fantasy.

    Of course, the only nod to this theme in the movie is made by Humperdink:
    “Not one couple in a century has that chance, no matter what the story books say.”

    Perhaps the DPR has a different business plan in the book than in the movie. I’m sure Morgenstern detailed it. He’s just so hard to read. :)


  15. Matthew Belinkie OTI Staff #

    Let me throw another wrinkle out there: why does Westley wait to seek out Buttercup? Let’s grant him that during his years of being part of Roberts’s crew, he had absolutely no chance of escape. There’s still no logical reason why he couldn’t take off to find Buttercup the SECOND he was put in charge of the ship. If this is a guy who is madly in love, and he knows that his beloved is living in near suicidal depression over his death, he should be trying to find his way home the instant he possibly can. He should at least write her a letter. But he doesn’t. He embarks on a successful career as a pirate.

    So we’re left with a damning coincidence: Westley JUST SO HAPPENS to seek out Buttercup mere days after the Prince publicly announces his engagement. The only possible conclusion I can draw is that Westley – like many young men – wasn’t in a huge hurry to commit to his serious girlfriend… until another dude moved in on her. He was probably always planning to find Buttercup EVENTUALLY, when he was sick of pirating and wenching and rich enough to afford his own island somewhere. But the thought that his ex might actually be MOVING ON, years after his death that he NEVER BOTHERED TO TELL HER DIDN’T HAPPEN, drives him absolutely crazy.

    I bet his whole plan when he starts chasing Vizzini isn’t to romance her, but to give her the world’s biggest guilt trip. “Not only am I still alive, I am STINKING RICH, and I have dozens of women DYING to marry me. So have fun with your little Prince. By the way, you’ve really let yourself go.” It’s only when she turns out to legitimately hate her fiancé that he waxes poetic about “true love” and decides they were meant to be together after all.

    Westley: what an asshole.


    • cat #

      Other than the fact that we wouldn’t have a story if he’d come back before she got engaged and it makes it all the more dramatic and allows him to say things like “Hear this now: I will always come for you. This is true love – you think this happens every day?”…

      The second he was put in charge of the ship he’d still have to steer it back from wherever it was which conceivably would take a good deal of time those days. He would have to be a pirate for at least a decent amount of time. Presumably he had no replacement and it would have been very ungrateful if he’d just been given the title and fled. He had a legacy to carry on. Also, he starts off as a farm boy. Even if he was happy to always reply “as you wish”, I think some part of him would have appreciated the chance to be able to amass a small fortune so he could provide for himself and Buttercup when he did get back and not have to work ever again (because presumably he has no skills other than being a farm boy…and clever…and good at fencing). There’s pride and status in being the DPR.

      Again, in terms of the story, he had to go away so he could learn to fight, protect and defend her, and…talk. They sent him away to become a more fully developed and interesting character. He comes back ready to play the dominant role in the relationship, always knowing what to say and how to reassure her as opposed to his earlier habit of responding to her orders.


    • Gab #

      Actually, allow me to twist your words ala some notorious news networks and use them for a different purpose:

      “…and rich enough to afford his own island somewhere.”

      That very well could be one of two keys to answering the question you pose, which is, Why did Westley wait? What does she call him? “Poor. Poor and perfect.” What if he didn’t think he was perfect? Didn’t he leave her initially to go make some money? So perhaps one reason he didn’t immediately seek her out when he became DPR was that he was, indeed, waiting to make more dubloons- but not out of selfishness or greed in the material sense, but to provide for her and feel worthy of her.

      And another reason could be that reputation of DPR’s. How strange would it look if DPR suddenly jumped ship (literally)? He needed to establish himself as DPR first and keep the reputation of the name intact. Then, hearing she was getting married, he decided To Hell With It and went after her.


    • Caroline #

      Well, he said he would always come for her. Apparently he expected her to really take it to heart. And take up some sort of hobby good for passing time.

      Though, it could be that he shows up not because the prince announced the engagement, but because the prince hired assassins. It could well be that the pirate/assassin want ads overlap a bit, and he sprang into action because he knew Vizzini was going to kill her.


  16. Dan from Canada #

    I guess the question comes down to whether “Never takes prisoners” means “Always kills everybody” or just “Never takes prisoners” Or more importantly, whether that needs to be a consistant policy across every Dread Pirate Roberts.

    Because remember, among the things that happens when the title passes is that they hire on a completely new crew so that the old captain can stay on as first mate for a while without anybody wising up.

    That means that while Ryan killed everybody on Wesley’s ship except Wesley, and may have been a bloodthirsty killer, there’s no reason, with a whole new crew, that Wesley couldn’t have simply applied the reputation to convince people to surrender without fighting, and just seize all their stuff and carry on.

    I also think that even if he hired on the kind of crew in keeping with the older more violent Dread Pirates Roberts, it wouldn’t be too hard to convince them to go ahead with accepting surrender from everybody without any risk of loss of life. Even wanting to go kill everybody just because they enjoy it carries the risk of injury or death, and a Dread Pirate Roberts promising tons of loot with no risk by just accepting surrenders would probably be pretyt popular.

    Everything he says to Buttercup on the subject of being DPR happens while he’s still in the act and trying to provoke information out of her to find out her true feelings, and isn’t necessarily indicative of anything beyond playing up the reputation.


  17. naomichan #

    Most of you are missing the point completely. The book came first. The book and the movie are completely different. The movie is a sappy love story for 80’s audiences. The book is a hardened satire. If you read any other Goldman novels you will find him poking fun at love; couples constantly bickering because they “love” each other. It’s not even about Wesley and Buttercup. It’s about modern couples. The first 31 pages of the book are about his home life and how messed up it is. How he’s attracted to the actress in the pool despite the fact that he’s married and has a kid. That is the real point. The movie is a watered down version of the book. (Also, people need to learn how to do math. We can calulate how long Wesley has be DPR. He’s been gone 5 yrs. He was Ryan’s valet 3yrs. So that give him 2yrs to be DPR. Things back in this time period took longer to do. We don’t know where he was when he became DPR. He could have been 2yrs away.)


  18. Lisa #

    I find it interesting that most of the comments are actually saying that he didn’t do it. We have no reason, based on what we see in the movies, to assume he didn’t do a lot of killing. We do have reason to assume he doesn’t leave people alive, as we see him doing so in the movie. Inigo and Fezzik could both potentially come back after him. It’s a lot safer to kill them. Yet he doesn’t. He can do so at his leisure, yet he leaves them.

    Vizzini, on the other hand, gets killed. It could be argued that Westley gives him a chance, but not a particularly fair one. It’s Vizzini who was the ring-leader of the gang, Vizzini who would have been ultimately responsible for her death, even if he could have brow-beaten one of his two minions into doing the actual dirty deed. There’s also a greater need to kill Vizzini, who’s the one most likely to come back and make his life difficult.

    Even the Prince is spared. Granted, not to have a happy life to look forward to necessarily, but we have seen him as a good spin doctor before, willing to manufacture negatives so that he can twist them to his own use. Is he really going to be less capable of that, just because he fell to one man’s bluff?

    Perhaps that’s why he thinks Inigo would be a better DPR. Inigo was able to kill his target, while Westley let his live. Inigo has, perhaps, the darker heart, less compunction about killing, whatever.

    Now, what Buttercup knows/suspects/asks about all that, we don’t know, because, well, it is a story for young boys, apparently, who often play pirates and soldiers and knights and all sorts of things where they kill other people, but fully expect the other people to get back up so they can start again. A deep female character doesn’t quite fit into that world, really.

    Gosh, I love this website! :D


    • Elise #

      I’ve read the book multiple times, and this is one of my favorite movies. I saw it initially when I was about five years old, so Westley (and Count Rugen, I’ll admit it) have loomed large in my imagination over the years.

      I agree with Matthew Belinkie – wtf didn’t Westley write? You can’t pick up a pen, Motherfucker?! I don’t think that he’s “just” testing her. He’s angry, he’s jealous, and he wants to punish her.

      I also think that he heard about the kidnapping and murder plans through the criminal network he would be a part of. “Leaves no survivors” = he has definitely killed people or been part of it in some way. I think a lot of it is that he’s built a reputation, but he learned to fence and built an immunity to iocaine powder, which means he’s had to fight to survive. However, he doesn’t kill Inigo or Fezzik. I think that he does kill people while marauding, but he’s not a cold-blooded murderer.

      It’s not Buttercup’s fault that Westley kept the fact that he was alive a secret to go off on adventures and make lots $$$. A girl’s got to eat, and she was just a peasant living on a farm. What were her prospects, exactly, in this type of pre-industrial society?

      What makes me sad is that in the book, when Humperdink & co show up after she and Westley make it through the Fire Swamp, she says “I can live without love,” which is some cold-ass shit. Westley saved her life multiple times, and he had presumably been the love of her life. To me, this her real betrayal.

      For a long time, I didn’t want them to remake this movie. But rewatching the PB in the years since the #metoo movement, it is in sore need of an update. To the person complaining that the movie isn’t true to the spirit of the book, do you realize that William Goldman wrote the screenplay?

      The story works both ways, I think, but I really want to see an updated version where Buttercup stands up for herself and also picks up the goddamn sword and stabs the ROUS for Christ’s sake!


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